Tertiary butyl naphthol and process for making



Patented Jan. 13,1931.

I UNITED STATES I PATENT OFFICE FRANZ KOEHIGSBERGE R, OF NEWARK, NEWJERSEY, ASSIGNOR TO DE HLS & STEIN, v OI NEWARK, NEW JERSEY um'rmmrIB'UTYL nnrnrnor. Am rnocnss roa MAKING 80 Drawing.

. Through the interaction of tertiary butyl chloride and naphthol I havemade a su stance which may be chemically described as tertiary butylnaphthol., To the best of my 3 knowled e this substance hasv never beenmade be ore, and is therefore entirely new.

I have found that the substance is useful as a plasticizer forcellulosic compounds, as a dyestufi component and as a pharmaceutical 1ochemical.

A, suitable method of preparing my new chemical substance is as follows:Mix together'144 grams beta naphthol, -14 grams aluminum chloride, and100 grams tertiary butyl chloride at room temperature. Warm v themixture gently-in a vessel equipped with reflux condenser untilevolution of hydrochloric acid -gas ceasesl Boil up the melted masstwice with water, each time pouring ofl? ao'tlie water: The resultingsubstance is subjected to a vacuum distillation in order to obtain thepurified product which I term 4- tertiary-butyl-B-naphthol and which hasa boiling point of about 14.6 degrees centigrade at 8 millimeterspressure. Its melting point. I havedetermined to be about 102 degreescentigrade.

It will of course be readily understood that tertiary butylnaphthol maybe made in other ways than that above described. For instance,other-butyl halides may be used or alpha naphthol may be usedinstead ofbeta naphtholor the given proportions may be varied or other catalyststhan aluminum chloride-may be employed which are capable of effectingtheFriedel'and Crafts reaction, such as zinc chloride. ferrous chloride.ferric chloride, stannic chloride and antimony pe'ntachloride. a

I have found that a chlorinated derivative of tertiary butyl naphthol isreadily made. through the interaction of tertiary butyl naphthol andsulfuryl chloride. To make.

this substance, add sulfuryl chloride drop by drop to a warmed quantityof tertiary butyl naphthol until the evolution ofhydrochloric acid gasceases. Boil up the mass twice with water and throw oi the water.Subject the resulting product to a vacuum distillation- 9 to obtain puretertiary butyl naphthol chlotert1ary butyl naphthol.

Application filed 0mm :2; 1022. Serial 10. 314,332.

ride; The number and position of the chlorine atoms entering the nucleushas not been definitely ascertained but it can be safely said that onechlorine atom enters the 1-position. Similarly, other halogenatedderivatives of tertiary butyl naphthol may be prepared. These derivedsubstances are to the best of my knowledge also new and they. are usefulfor purposes similar to those mentioned for v I claim: a

1. As a new article of manufacture, a substance of the class consistingof tertiary butyl naphthol and its halo enated derivatives.

2. As a new article 0 manufacture, a chemical substance comprising thereaction product of a butylhalide and a naphthol.

3. As a new article of manufacture, a 4-tertiary-butyl-fimaphthol.

4. As a new article of manufacture, a halogenated derivative of tertiarybutyl naphthol. u

- 5. The herein described process of manufacturing a tertiary butylnaphthol which comprises reacting a but 1 halide with a naphthol in thepresence 0 a catalyst capable of efiecting the Friedel'and Craftsreaction.

6. The, herein described process of manufacturing a tertiary butylnaphthol which comprises reacting a tertiary butyl chloride with anaphthol in the presence of a catalyst capable of elfecting the'Friedeland Crafts reaction. I

7. The herein described rocess of manufacing a tertiary butyl nap tholwhich'com-- prises reactin a tert ary butyl chloride with eta naphtho inthe presence of a catalyst capable of eifectin'g the Friedel and Craftsreaction. 5

8. The hereindescribed' process of manu jecting the resulting substanceto vacuum, distillation.

9. The herein described processof manufacturing a chlorinated derivativeof ter-' tiary butyl chloride, which comprises reactin tertiary butylnaphthol and sulfuryl ch oride. I

10. The herein described process of manufacturing a tertiary butylnaphthol which comprises reacting -a butyl halide with a'. Y naphthol. e11. The herein described process of manufacturing a tertiary butylnaphthol which comprises reacting a tertiary butyl chloride with anaphthol.

In testimony'whereof II have aflixed my signature. E FRANZKOENIGSBERGER.

